What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $348. Additional round-trip tickets that might be worth considering are offered by Porter Airlines and KLM, with the lowest prices starting at $387 and $459, respectively. These flights start at 34% lower than the current average price 3 months from now.

What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

One-way options have recently been found by users for as low as $211 on WestJet. Other airlines that offer cheap prices include Air Canada from $244 and Delta from $273 one-way.

What is the cheapest day to fly from Chicago to Winnipeg?

Travelers seeking maximum savings on their Chicago to Winnipeg flight should consider departing on Saturday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the cheapest flights from Chicago to Winnipeg?

The cheapest flight price from Chicago to Winnipeg is $107. On average you can expect to pay $734. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $247.

What are the most reliable airlines from Chicago to Winnipeg?

The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (69%), Air Canada (69%) and United Airlines (69%).

What is the cheapest day to fly round-trip from Chicago to Winnipeg?

Friday flights are generally found to be more expensive for flights from Chicago to Winnipeg. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Winnipeg.

What is the cheapest month to fly from Chicago to Winnipeg?

March can be a great time to fly to Winnipeg from Chicago with a flight ticket averaging about $535. Cheapflights users have found deals in the month of March for as cheap as $216. The most expensive prices can be found in the month of February.

Most accurate provider : When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

What airport do you fly into for flights to Winnipeg from Chicago?

Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 3 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Chicago to Winnipeg?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

Can I find deals for business class flights from Chicago to Winnipeg?

Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$133+ Flights from Chicago to Winnipeg

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Chicago to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Winnipeg

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$258 (Kiwi.com)
One-way from	$137 (Kiwi.com)
Popular in	February
Cheapest in	March
Average price	$752
Good round-trip deal	$594 or less

Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.

Search Deals

Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.

Search Deals

From Chicago (CHI) to Winnipeg

Search Deals

One-way flight from Chicago (CHI) to Winnipeg

Search Deals

High demand for flights, 20% potential price rise

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in February 2025

Search Deals

Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.

Search Deals

Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

Thu 4/104:45 pmORD - YWG

1 stop7h 59mWestJet

Sun 4/138:15 amYWG - ORD

1 stop7h 41mWestJet

Deal found 2/21

$246

Tue 6/36:00 amORD - YWG

1 stop10h 28mMultiple Airlines

Mon 6/98:30 amYWG - ORD

1 stop8h 14mMultiple Airlines

Deal found 2/22

$258

Tue 4/810:13 amMDW - YWG

2 stops14h 31mMultiple Airlines

Tue 4/157:30 amYWG - MDW

1 stop12h 15mMultiple Airlines

Deal found 2/22

$300

Thu 3/275:35 pmMDW - YWG

2 stops24h 24mPorter Airlines

Mon 3/315:00 amYWG - MDW

1 stop11h 40mPorter Airlines

Deal found 2/22

$387

Tue 4/87:09 pmMDW - YWG

1 stop16h 51mKLM

Tue 4/155:43 pmYWG - MDW

1 stop15h 57mKLM

Deal found 2/22

$459

Wed 4/99:30 amORD - YWG

1 stop7h 23mDelta

Wed 4/168:35 amYWG - ORD

1 stop8h 54mDelta

Deal found 2/21

$461

Fri 3/219:12 pmORD - YWG

1 stop11h 16mAir Canada

Sun 3/237:30 amYWG - ORD

1 stop7h 21mAir Canada

Deal found 2/22

$499

Tue 4/810:25 amMDW - YWG

1 stop6h 28mDelta

Tue 4/156:40 amYWG - MDW

1 stop7h 42mDelta

Deal found 2/22

$517

Sat 5/317:10 amORD - YWG

1 stop5h 59mUnited Airlines

Sat 5/314:25 pmYWG - ORD

1 stop8h 00mUnited Airlines

Deal found 2/20

$558

Fri 4/259:20 amMDW - YWG

2 stops9h 49mWestJet

Mon 4/289:00 amYWG - MDW

1 stop8h 59mWestJet

Deal found 2/22

$668

Best flights from Chicago to Winnipeg
Discover carefully curated flight deals from Chicago to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 23, 2025.

Tue 6/36:00 amORD - YWG

1 stop10h 28mMultiple Airlines

Mon 6/98:30 amYWG - ORD

1 stop8h 14mMultiple Airlines

Deal found 2/22

$258

Wed 6/111:40 pmORD - YWG

1 stop7h 46mWestJet

Mon 6/169:05 pmYWG - ORD

1 stop19h 39mWestJet

Deal found 2/22

$348

Thu 3/275:35 pmMDW - YWG

2 stops24h 24mPorter Airlines

Mon 3/315:00 amYWG - MDW

1 stop11h 40mPorter Airlines

Deal found 2/22

$387

Tue 4/87:09 pmMDW - YWG

1 stop16h 51mKLM

Tue 4/155:43 pmYWG - MDW

1 stop15h 57mKLM

Deal found 2/22

$459

Fri 3/219:12 pmORD - YWG

1 stop11h 16mAir Canada

Sun 3/237:30 amYWG - ORD

1 stop7h 21mAir Canada

Deal found 2/22

$499

Tue 4/810:25 amMDW - YWG

1 stop6h 28mDelta

Tue 4/156:40 amYWG - MDW

1 stop7h 42mDelta

Deal found 2/22

$517

Sat 5/315:02 amORD - YWG

1 stop8h 07mUnited Airlines

Sat 5/314:25 pmYWG - ORD

1 stop8h 00mUnited Airlines

Deal found 2/22

$558

Tue 4/810:13 amMDW - YWG

2 stops14h 31mMultiple Airlines

Tue 4/157:30 amYWG - MDW

1 stop12h 15mMultiple Airlines

Deal found 2/22

$300

Mon 3/241:26 pmORD - YWG

2 stops10h 03mDelta

Mon 3/318:50 amYWG - ORD

2 stops9h 31mDelta

Deal found 2/22

$576

Fri 4/259:20 amMDW - YWG

2 stops9h 49mWestJet

Mon 4/289:00 amYWG - MDW

1 stop8h 59mWestJet

Deal found 2/22

$668

Last-minute flights from Chicago to Winnipeg
Discover last-minute flight deals from Chicago to Winnipeg. Data last updated February 23, 2025 and is based on user searches.

Mon 2/241:08 amORD - YWG

2 stops34h 14mAeromexico

Wed 2/268:00 pmYWG - ORD

2 stops27h 21mAeromexico

Deal found 2/21

$2,906

Sun 3/24:45 pmORD - YWG

1 stop16h 25mWestJet

Thu 3/68:15 amYWG - ORD

1 stop7h 41mWestJet

Deal found 2/21

$299

Sun 3/25:35 pmMDW - YWG

2 stops24h 24mPorter Airlines

Thu 3/611:35 amYWG - MDW

2 stops22h 45mPorter Airlines

Deal found 2/21

$815

Sun 3/210:19 amMDW - YWG

1 stop6h 24mWestJet

Thu 3/66:40 amYWG - MDW

1 stop6h 02mWestJet

Deal found 2/21

$926

Mon 3/33:14 pmORD - YWG

2 stops23h 54mMultiple Airlines

Sun 3/96:20 amYWG - ORD

2 stops24h 22mMultiple Airlines

Deal found 2/22

$430

Mon 3/312:58 pmORD - YWG

Nonstop2h 30mAir Canada

Sun 3/911:55 amYWG - ORD

1 stop7h 42mAir Canada

Deal found 2/22

$794

Mon 3/312:58 pmORD - YWG

Nonstop2h 30mUnited Airlines

Sun 3/92:15 pmYWG - ORD

Nonstop2h 22mUnited Airlines

Deal found 2/22

$810

Wed 3/1211:15 amMDW - YWG

1 stop13h 19mMultiple Airlines

Sun 3/168:00 pmYWG - MDW

1 stop14h 20mMultiple Airlines

Deal found 2/21

$522

Fri 3/219:12 pmORD - YWG

1 stop11h 16mAir Canada

Sun 3/237:30 amYWG - ORD

1 stop7h 21mAir Canada

Deal found 2/22

$499

Sat 3/2212:58 pmORD - YWG

Nonstop2h 30mUnited Airlines

Mon 3/242:15 pmYWG - ORD

Nonstop2h 22mUnited Airlines

Deal found 2/22

$595

Sat 3/2211:27 amMDW - YWG

1 stop5h 26mWestJet

Mon 3/2412:53 pmYWG - MDW

1 stop5h 25mWestJet

Deal found 2/22

$695

Mon 3/241:26 pmORD - YWG

2 stops10h 03mDelta

Mon 3/318:50 amYWG - ORD

2 stops9h 31mDelta

Deal found 2/22

$576

One-way flights from Chicago to Winnipeg
Search for one-way flight options from Chicago to Winnipeg. Find affordable one-way fares based on user searches. Data last updated February 23, 2025.

Fri 5/26:20 amORD - YWG

1 stop10h 08mMultiple Airlines

Deal found 2/21

$137

Fri 5/26:15 amMDW - YWG

2 stops16h 56mMultiple Airlines

Deal found 2/21

$137

Sun 4/64:45 pmORD - YWG

2 stops15h 38mWestJet

Deal found 2/22

$211

Sun 4/68:25 pmORD - YWG

1 stop14h 37mAir Canada

Deal found 2/22

$244

Mon 6/301:00 pmMDW - YWG

2 stops10h 22mDelta

Deal found 2/20

$273

Sun 4/611:15 amMDW - YWG

2 stops30h 44mPorter Airlines

Deal found 2/22

$284

Thu 7/177:30 amORD - YWG

2 stops15h 53mUnited Airlines

Deal found 2/22

$294

Fri 3/141:26 pmORD - YWG

2 stops10h 03mDelta

Deal found 2/22

$304

Thu 7/179:20 amMDW - YWG

2 stops14h 21mWestJet

Deal found 2/21

$326

Find flights from Chicago to Winnipeg within your budget

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Thu 4/10

4:45 pm-12:44 am

1 stop7h 59m

Winnipeg

Sun 4/13

8:15 am-3:56 pm

1 stop7h 41m

$246

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Tue 6/3

6:00 am-4:28 pm

1 stop10h 28m

Winnipeg

Mon 6/9

8:30 am-4:44 pm

1 stop8h 14m

$258

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 4/8

10:13 am-12:44 am

2 stops14h 31m

Winnipeg

Tue 4/15

7:30 am-7:45 pm

1 stop12h 15m

$300

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Thu 3/27

5:35 pm-5:59 pm

2 stops24h 24m

Winnipeg

Mon 3/31

5:00 am-4:40 pm

1 stop11h 40m

$387

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 4/8

7:09 pm-12:00 pm

1 stop16h 51m

Winnipeg

Tue 4/15

5:43 pm-9:40 am

1 stop15h 57m

$459

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Wed 4/9

9:30 am-4:53 pm

1 stop7h 23m

Winnipeg

Wed 4/16

8:35 am-5:29 pm

1 stop8h 54m

$461

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Fri 3/21

9:12 pm-8:28 am

1 stop11h 16m

Winnipeg

Sun 3/23

7:30 am-2:51 pm

1 stop7h 21m

$499

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Tue 4/8

10:25 am-4:53 pm

1 stop6h 28m

Winnipeg

Tue 4/15

6:40 am-2:22 pm

1 stop7h 42m

$517

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

Sat 5/31

7:10 am-1:09 pm

1 stop5h 59m

Winnipeg

Sat 5/31

4:25 pm-12:25 am

1 stop8h 00m

$558

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

Fri 4/25

9:20 am-7:09 pm

2 stops9h 49m

Winnipeg

Mon 4/28

9:00 am-5:59 pm

1 stop8h 59m

$668

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 19 results

Compare providers for flights from Chicago to Winnipeg

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in February.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Winnipeg

Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $508). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 13% on airfare.

Weekly flight availability from Chicago to Winnipeg

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

See what other customers who have flown with Delta, Porter Airlines and KLM from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Delta

8.0

Very good

8,203 reviews

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Porter Airlines

7.9

Good

277 reviews

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

KLM

7.8

Good

1,332 reviews

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

United Airlines

7.4

Good

8,754 reviews

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

WestJet

7.2

Good

2,796 reviews

Delta

8.0

Very good

8,203 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

What airport do you fly into for flights to Winnipeg from Chicago?
Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 3 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.
What are the cheapest airlines flying from Chicago to Winnipeg round-trip?
Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $348. Additional round-trip tickets that might be worth considering are offered by Porter Airlines and KLM, with the lowest prices starting at $387 and $459, respectively. These flights start at 34% lower than the current average price 3 months from now.
What are the cheapest airlines to fly from Chicago to Winnipeg one-way?
One-way options have recently been found by users for as low as $211 on WestJet. Other airlines that offer cheap prices include Air Canada from $244 and Delta from $273 one-way.
What are the most reliable airlines from Chicago to Winnipeg?
The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (69%), Air Canada (69%) and United Airlines (69%).
What are the cheapest flights from Chicago to Winnipeg?
The cheapest flight price from Chicago to Winnipeg is $107. On average you can expect to pay $734. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $247.
Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?
Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Chicago to Winnipeg?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.
Can I find deals for business class flights from Chicago to Winnipeg?
Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Chicago to Winnipeg?
Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $508). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Winnipeg

O'Hare Intl to Winnipeg flights

Midway to Winnipeg flights

St. Louis to Winnipeg flights

Other flights to Winnipeg

Top 2 airlines flying from Chicago to Winnipeg

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	Cheapest$235	Average$617	FlexibilityNo cancel fee	On-time67%
United Airlines	Cheapest$535	Average$710	FlexibilityNo cancel fee	On-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$133+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Winnipeg with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Chicago to Winnipeg

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to WinnipegExplore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

Find flights from Chicago to Winnipeg within your budget

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in February.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.

Travel insights for flights from Chicago to Winnipeg

Get recent, data-driven insights about flights from Chicago to Winnipeg including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Chicago to Winnipeg?

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 23, 2025.

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 23, 2025.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

Reviews of airlines servicing Winnipeg

See what other customers who have flown with Delta, Porter Airlines and KLM from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to Winnipeg from Chicago?

What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

What are the most reliable airlines from Chicago to Winnipeg?

What are the cheapest flights from Chicago to Winnipeg?

Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

How can I find direct flights from Chicago to Winnipeg?

Can I find deals for business class flights from Chicago to Winnipeg?

What is the cheapest month to book a flight from Chicago to Winnipeg?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Chicago to Winnipeg

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.